1,3,5-三(苯基)-4'-三膦酸苯 | 1045720-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3,5-三(苯基)-4'-三膦酸苯
• 中文别名: P,P'-[5'-(4-膦酰基苯基)[1,1':3',1''-三联苯]-4,4''-二基]双[膦酸
• 英文名称: 1,3,5-tris(4-phosphonophenyl)benzene
• 英文别名: [4-[3,5-Bis(4-phosphonophenyl)phenyl]phenyl]phosphonic acid；[4-[3,5-bis(4-phosphonophenyl)phenyl]phenyl]phosphonic acid
• CAS: 1045720-71-5
• 化学式: C₂₄H₂₁O₉P₃
• 分子量: 546.347
• InChiKey: SJPQASSBALSRNU-UHFFFAOYSA-N

物化性质

• 熔点：
  335-345 °C
• 沸点：
  878.4±75.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  173
• 氢给体数：
  6
• 氢受体数：
  9

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  tin (IV) chloride pentahydrate 、 1,3,5-三(苯基)-4'-三膦酸苯 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 50.0h， 生成 Sn(1,3,5-tris(4-phosphonophenyl)benzene(-4H))*(H₂O)_4.5
  参考文献：
  名称：

  Enhancing Order and Porosity in a Highly Robust Tin(IV) Triphosphonate Framework

  摘要：

  Metal organic frameworks (MOFs) are noted for crystallinity, stability, and porosity. For many industrial challenges though, beyond stability to pore activation, porous materials require high thermal and moisture stability. Here, we report a Sn(W) triphosphonate framework, CALF-28, that is highly robust and porous. CALF-28 was designed based on the known structure of a divalent metal phosphonate that was 2-fold interpenetrated. It has strong sustaining interactions but consequently rapidly precipitates, compromising crystallinity. Using methods to enhance order, and by analogy to the M(II) analogue, insights to the structure are ascertained and corroborated by PXRD and gas sorption analysis. CALF-28 has a surface area >500 m(2)/g and is stable in water.

  DOI：

  10.1021/ic400274e
• 作为产物：
  描述：

  1,3,5-tris(diisopropyl phenyl-4-phosphonato)benzene 在 盐酸 、 水 作用下， 以 丙酮 为溶剂， 以74.28%的产率得到1,3,5-三(苯基)-4'-三膦酸苯
  参考文献：
  名称：

  多取代芳基膦酸酯的可扩展合成：探索等理论膨胀的极限和新型三氮烯基膦酸酯的合成

  摘要：

  摘要 新型多取代芳基膦酸酯化合物的开发有望成为具有优异孔隙率和气体吸附性能的金属有机骨架 (MOF) 材料的新构件。我们证明了钯催化的 Hirao 交叉偶联反应在取代膦酸酯的合成中的效率；然而，尝试通过 4-(4'-溴苯基) 苯乙酮的环化制备具有等距扩展的衍生物的尝试导致极低的产率，并分离出二聚体中间体。从头算计算表明，虽然苯乙酮的三聚是放热的，但 4-苯基苯乙酮的三聚是吸热的。相比之下，4-(4'-溴苯基) 苄腈的环化是放热的，并允许形成适当的膦酸。苄腈方法还允许形成具有高位阻的邻甲基衍生物。本文报道的所有多取代芳基膦酸酯化合物都可以在多克规模上制备，使研究人员能够为膦酸酯 MOF 提供更广泛的构建模块。图形概要

  DOI：

  10.1080/10426507.2019.1673750

文献信息

• The use of a rigid tritopic phosphonic ligand for the synthesis of a robust honeycomb-like layered zirconium phosphonate framework
  作者：Marco Taddei、Ferdinando Costantino、Riccardo Vivani、Stefano Sabatini、Sang-Ho Lim、Seth M. Cohen

  DOI：10.1039/c4cc01253d

  日期：——

  1,3,5-Tris(4-phosphonophenyl)benzene was synthesized via a microwave heating assisted route and was subsequently used for the preparation of a new zirconium phosphonate with honeycomb-like structure displaying remarkable thermal stability and hydrolysis resistance.

  1,3,5-三(4-磷酸苯基)苯是通过微波加热辅助路线合成的，并随后用于制备具有蜂窝状结构的新锆磷酸盐，表现出显著的热稳定性和抗水解性。
• Synthesis and characterisation of the porous zinc phosphonate [Zn₂(H₂PPB)(H₂O)₂]·xH₂O
  作者：N. Hermer、H. Reinsch、P. Mayer、N. Stock

  DOI：10.1039/c6ce01580h

  日期：——

  The synthesis, structure and properties of the new microporous zinc phosphonate [Zn2(H2PPB)(H2O)2]·xH2O (denoted as CAU-25, CAU stands for Christian-Albrechts-University) are presented. The crystal structure was determined by combining single crystal and powder X-ray diffraction data. The final refinement was carried out by using the Rietveld method. The structure contains one-dimensional channels between dense, corrugated, hydrogen bonded layers with a diameter of approximately 5 Å. While N2 uptake was not observed at 77 K, CO2 and H2O uptakes were measured at 298 K.

  新型微孔膦酸锌[Zn2(H2PPB)(H2O)2]·xH2O（简称CAU-25，CAU代表Christian-Albrechts-University）的合成、结构与性质得到阐述。通过单晶和粉末X射线衍射数据的结合，确定了其晶体结构。最终的精修采用Rietveld方法进行。该结构中，致密、波纹状、通过氢键连接的层之间存在直径约为5 Å的一维通道。在77K下未观察到N2的吸附，但在298K下测得了CO2和H2O的吸附量。
• A microporous alkaline-earth phosphonate sustained by one-dimensional inorganic and organic units
  作者：Ramanathan Vaidhyanathan、Amir H Mahmoudkhani、George KH Shimizu

  DOI：10.1139/v08-130

  日期：2009.1.1

  The single-crystal X-ray structure of a microporous alkaline-earth phosphonate incorporating a new triphosphonate ligand is presented. Sr₂(H₂L)(CH₃OH)(H₂O)₄, where L = 1,3,5-tris(4-phosphonophenyl)benzene, crystallizes in triclinic space group P-1 (a = 6.9230(4) Å, b = 15.3370(9) Å, c = 16.1930(11) Å, α = 62.201(3)°, β = 85.288(4)°, γ = 86.665(4)°). The solid is sustained by cooperative interactions between both one-dimensional inorganic and organic columns and forms a two-fold interpenetrated microporous structure. Gas and vapour sorption experiments confirm the microporosity. Based upon the sustaining interactions, this compound can serve as a model for more porous structures as extension of its structure disfavours further interpenetration.Key words: metal–organic framework, coordination polymer, phosphonate, microporous, alkaline earth.

  本文展示了一种含有新型三膦酸酯配体的微孔碱土膦酸盐的单晶 X 射线结构。Sr2(H2L)(CH3OH)(H2O)4（其中 L = 1,3,5-三(4-膦酰基苯基)苯）在三linic 空间群 P-1 中结晶（a = 6.9230(4) Å，b = 15.3370(9) Å，c = 16.1930(11) Å，α = 62.201(3)°，β = 85.288(4)°，γ = 86.665(4)°）。这种固体由一维无机柱和有机柱之间的协同作用维持，并形成了双重互穿微孔结构。气体和蒸汽吸附实验证实了这种微孔结构。关键词：金属有机框架；配位聚合物；膦酸盐；微孔；碱土。
• Multifunctionality in an Ion-Exchanged Porous Metal–Organic Framework
  作者：Sérgio M. F. Vilela、Jorge A. R. Navarro、Paula Barbosa、Ricardo F. Mendes、Germán Pérez-Sánchez、Harriott Nowell、Duarte Ananias、Filipe Figueiredo、José R. B. Gomes、João P. C. Tomé、Filipe A. Almeida Paz

  DOI：10.1021/jacs.0c10421

  日期：2021.1.27

  however, not robust enough to be used as multifunctional materials. This is typically the case of Metal-Organic Frameworks (MOFs) which rarely combine several different excellent functionalities into the same material. In this report we describe the simple acid-base postsynthetic modification of isotypical porous rare-earth-phosphonate MOFs into a truly multifunctional system, maintaining the original porosity

  多孔坚固材料通常是几种工业过程的主要选择。然而，许多这些化合物不够坚固，无法用作多功能材料。这通常是金属有机框架 (MOF) 的情况，它很少将几种不同的出色功能结合到同一材料中。在本报告中，我们描述了同型多孔稀土膦酸酯 MOF 的简单酸碱合成后改性成一个真正的多功能系统，保持原始孔隙率特征：[Ln(H3pptd)]·xSolvent [其中 Ln3+ = Y3+ (1) 和(Y0.95Eu0.05)3+ (1_Eu)] 通过浸入粉末转化为 [K3Ln(pptd)]·zSolvent [其中 Ln3+ = Y3+ (1K) 和 (Y0.95Eu0.05)3+ (1K_Eu)]将 1 和 1_Eu 加入 KOH 乙醇溶液中 48 小时。K+ 交换的 Eu3+ 基材料在 CO2 吸附方面表现出相当大的提升，能够重复使用多个连续循环。它可以从由 CH4、CO2 和 C2H2 组成的复杂三元气体混合物中进一步分离
• Phosphonates Meet Metal−Organic Frameworks: Towards CO ₂ Adsorption
  作者：Cleiser Thiago P. da Silva、Ashlee J. Howarth、Martino Rimoldi、Timur Islamoglu、Andrelson W. Rinaldi、Joseph T. Hupp

  DOI：10.1002/ijch.201800129

  日期：2018.10

  (BET) surface area of the “unconventional metal−organic framework” (UMOF) is measured to be ∼900 m2/g, after following an appropriate activation protocol. Diffuse reflectance infrared Fourier transform spectroscopy (DRIFTS) shows that the material bears a free −OH functionality on the phosphonate linker that may interact with CO2. CO2 adsorption isotherms were collected and a measured heat of adsorption

  在这里，我们报告在溶剂热条件下合成的一种新型的高微孔膦酸锆材料。在遵循适当的激活方案后，“非常规金属-有机骨架”（UMOF）的特定Brunauer-Emmett-Teller（BET）表面积经测量为约900 m 2 / g。漫反射红外傅里叶变换光谱法（DRIFTS）表明，该材料在膦酸酯连接基上带有可能与CO 2相互作用的游离-OH官能团。收集CO 2吸附等温线，并获得测得的31 kJ / mol的吸附热。另外，CO 2，N 2和CH 4的吸附等温线在298 K的条件下，结合理想吸附溶液理论（IAST）表明，可以预期该材料显示出对CO 2吸收比N 2或CH 4高的选择性。